


Wrong End of the Deal

by SuperWhoLock_12



Category: Supernatural
Genre: Bondage, Demon Deals, Demon Dean, Demon Dean Winchester, Explicit Sexual Content, Extremely Dubious Consent, F/M, Oral Sex, Rape/Non-con Elements, Reader-Insert
Language: English
Status: Completed
Published: 2016-08-16
Updated: 2016-08-16
Packaged: 2018-08-09 06:20:28
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 4,723
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7789984
Author URL: https://archiveofourown.org/users/SuperWhoLock_12/pseuds/SuperWhoLock_12
Summary: <blockquote class="userstuff">
              <p>You just wanted a drink at your favorite bar, but no, your monster-hunting ex had to pick THAT one to hang out in when he rolled into town. You weren't interested in anything but a drink and a friendly chat, but Dean seems to want more.</p>
<p>And he doesn't appear inclined to take no for an answer...</p>
            </blockquote>





	Wrong End of the Deal

**Author's Note:**

> I swear I'm working on KYP, y'all, but this was a plot bunny that grabbed me by the hair and wouldn't let go.

It had been a long day at work. One of those days that made you wonder why you'd picked your field to go into; didn't your mom tell you that it meant nothing but long hours and low pay? Sighing, you finished your cocktail and nodded at the bartender. 

“Let me get another one, Jon.” _Thank God it's Friday._

You'd been coming to this bar for long enough that Jon knew you, and he shot you a sympathetic look as he mixed your drink. “Another bad one, Y/N?”

You nodded. “Yeah. Why did I think this job was a good idea?” you asked rhetorically.

“Because it must pay really well, darlin',” Jon replied, placing the fresh drink in front of you and removing the empty glass. Before you could respond and tell him that, in fact, lobbying against Big Pharma paid next to nothing, a rough male voice called out for beer at the other end of the bar and Jon moved away to fulfill the order.

You exhaled and scrubbed your hands over your face, remembering just in time that you were wearing makeup and managing not to make yourself look like a raccoon. _This is the last drink,_ you told yourself. _Any more and I'll have to Uber home._

Lost in your thoughts, you didn't notice that the man at the far end of the bar was staring at you, recognition slowly spreading across his face. It was a complete shock when he called out, “Y/N! Is that you? What are you doing here?”

You jumped, almost falling off your barstool. _Whoops. Maybe it's Uber after all._ You squinted in the direction of the voice, then almost fell off the barstool again when you recognized its source. “Dean? Dean Winchester?”

Your ex got up and headed towards you, flashing that stunningly attractive smile that had made you fall into his arms years ago. You felt your knees go weak, then sternly reminded yourself that you had broken the relationship off for a reason; unfortunately, with Dean getting steadily closer, it was hard to remember what that reason was...

You jerked yourself back to the present as Dean slid onto the stool on your right. “How're you doin', Y/N?”

“I'm – I'm good,” you managed to get out. “What about you?” Frowning, you scanned the bar for Dean's 6'4” monster-hunting partner-in-crime. “Where's Sam?”

A shadow seemed to cross Dean's face, but it was immediately covered by a blinding grin. “We've decided we need to split up for a while, you know? There is a such thing as too much brother-ness.” He frowned. “Is that a word?”

“No, no it's not,” you replied absently. Since when was there a such thing as too much brotherly togetherness for the Winchesters? When you and Dean had been together, you'd seen Sam almost as much as your boyfriend, since they never went anywhere without the other.

“Well, you would know,” Dean said cheerfully. “You've always been the smart one.”

The two of you spent the next thirty minutes talking about some of the changes in your life before the conversation veered around to Dean. “Well, like I said, Sammy and me are takin' some time apart,” he said, fiddling with his beer bottle. “I got – cursed, I guess, last year, and I did some things he didn't like, and he did some things I didn't like, and we decided we should split for a while, y'know?”

“Yeah,” you said, spinning your empty glass around on the bar – _was this drink number four? Five?_ “Sometimes it's the people we love the most that we need space from. I know with my fiance -”

“Wait,” Dean interrupted. “You're _engaged?!_ ”

You blushed and held up your left hand, displaying the modest ring. “I met him a couple of years ago, and we just kinda clicked, you know? We're getting married in three weeks and two days.” You blushed harder. “Not like I'm counting down or anything.”

“Yeah, Y/N, totally not counting down,” Dean said, rolling his eyes. Then those same eyes darkened, and you felt a hand rest on your knee. “What do you say to one last fling? Before you get married, for old times sake?”

Your jaw dropped open and you stared at him. You knew Dean was a bit of a playboy, but - “What the hell – no! I _love_ him, Dean! I'm not going to destroy my relationship just because you roll into town and want an easy fuck!”

“Yeah?” Dean said lowly, and the hand on your knee inched upwards. “I bet he's not as good in bed as I am.” The tip of his tongue slid out and moistened his bottom lip and you stared at it, remembering the things he could do with it that had made you _scream_ -

“Better than you,” you sneered, alcohol making you brave. You grabbed his wrist, trying to move his hand off your leg, but it didn't budge. “Dean, let go of me!” He tightened his grip, pressing into your thigh with enough force to leave bruises, before he abruptly yanked the hand away.

“Fine,” he growled. 

You looked at him with shock and a little bit of fear. What the hell was that? “I think I'd better go,” you said, inching away from him. “Jon?”

You paid your tab and walked out the door, leaving Dean nursing yet another beer at the bar. When the cold air hit you, though, you realized just how drunk you were. “Shit,” you muttered to yourself. “I'm gonna have to call a cab or get an Uber or something.” You went over to your car and slid into the driver's seat to get out of the wind, already pulling up the Uber app.

Some sixth sense made you look up from your phone, but you only had enough time to see Dean's reflection in the rearview mirror before everything went black.

~*~*~*~*~*~*~*~*~

You woke up slowly, as you always did, grimacing at the taste in your mouth. _Ugh, I definitely drank too much last night,_ you thought, moving to get up and go to the bathroom to brush your teeth - 

\- except you couldn't. You couldn't move at all.  
Your eyes flew open and you looked around, remembering the night before. You were in a room you'd never seen before, tied – you tugged experimentally – quite securely spread-eagle to a four poster bed. Thankfully, you were still wearing your work clothes you'd had on at the bar, minus your suit jacket, and you breathed out a silent sigh of relief before beginning to jerk at your bonds in earnest. Nothing gave, and you yanked harder and harder as panic began to overwhelm you. Finally, you opened your mouth and screamed “HELP! HELP ME!” There was no response, no sound from anything other than your own terrified breathing and rapid heartbeat, and you returned to pulling frantically at the ropes that bound you to the bedstead.

Eventually you gave up and began to slowly subside, accepting that, for right now, there was nothing you could do to escape. You began to cast your eyes around the room, looking for some clue as to where you were or how you'd gotten there, but there was nothing identifying in your line of sight. Just a plain bedroom, painted beige, with a small chest of drawers near the foot of the bed.

You heard a door slam, disconcertingly nearby, and tensed. Sure enough, a few moments later the door opened and Dean walked in. He was still wearing the black t-shirt and red button down he'd had on at the bar, along with the standard Winchester uniform of jeans and boots. He moved quietly, almost silently, which was unusual for him – Dean tended to be loud and fast, and this liquid, animal grace was unfamiliar and a bit frightening.

When he sat down on the edge of the bed next to you and traced his fingers along your ribcage, your wariness was drowned in a flood of outrage. “Dean, what the hell do you think you're doing?! This isn't funny! Let me go this _instant_ or I swear to _God_ -” He waved his hand, and your jaw clicked shut against your will. The tall man leaned forward and smiled, then brushed a finger across the seam of your closed lips as he looked into your fearful eyes.

“Sweetheart, God has nothing to do with this.” Those beautiful green eyes flashed black, and you drew a sharp breath in through your nose. _Possessed. Oh shit, he's possessed._ As though he could hear your thoughts, Dean laughed and sat back, eyes going back to green. “I'm not possessed, Y/N. This is still all me, one hundred percent Dean Winchester. I just got a few quirks and a new allegiance now.”

The invisible grip on your jaw loosened, and you spat, “Allegiance to Hell? Allegiance to _Crowley?_ ”

Dean nodded. “Absolutely. In fact, that's the reason I'm here. Turns out, the King of Hell doesn't much like what your little firm's been doing. More people sell their souls for a cure if the cure is too expensive for them, so Crowley needs those prices to stay high – and you've been having a little too much success at getting gouging laws passed.” He shrugged. “Or so it was explained to me.” Before you could respond, he continued. “See, that fiance of yours? _He's_ possessed. He was supposed to distract you, to get you to focus less on your job, but it wasn't working, so Crowley dispatched his favorite – and only – Knight of Hell to kill you. Now,” his eyes flashed black again, “you wanna guess who that Knight of Hell is?”

Your brain short-circuited into panic and you began thrashing on the bed, jerking against your bonds and paying no heed to the rope burn you were getting on your wrists and ankles as you struggled. Dean stayed on the bed, arms crossed, and watched you fight, but you were completely oblivious to anything but finding and taking advantage of any slight slack in the ropes. Finally, after what seemed an eternity, you gave up and screamed, “Do it! Kill me, if you're going to! Kill me! DO IT!” The demon just sat there with an unearthly stillness, watching calmly as your shrieking devolved into tears.

Finally, after your sobs had turned to sniffles and finally to a resigned silence, Dean spoke. “As I was saying, Crowley sent me to kill you, and I came here planning to do just that. After all, what's more fun than killing an ex who broke your heart?” He grinned, flashing his white teeth, before continuing. “Then I saw you, across the bar, and I thought, well, there's one thing more fun than killing...” his smile widened, and you tried not to hyperventilate.

“Rape,” you whispered.

Dean waved his hand in dismissal. “Please. It's not rape if you beg me for it.” He straddled your hips and leaned down until his lips were almost touching yours, and you had to fight not to turn your head away. You could feel his warm breath against your mouth as he whispered, “And you will beg.”

You took a deep breath to steady yourself, then whispered back, “I hate to break it to you, but knowing that you're going to kill me doesn't inspire me to beg you for anything.”

Dean moved around and nipped at your neck with sharp teeth, causing you to tense and tug involuntarily at your bonds. “Wanna bet?” he hissed in your ear.

“Yeah, actually,” you answered firmly. “No way in hell – pardon the pun – am I going to get any sort of enjoyment out of sex with a demon who's planning on murdering me as soon as he comes.”

Dean sighed heavily against your neck before sitting back. “Fine. Let's make a deal.” You looked at him, eyes narrowed, but he put his hands up. “Seriously. And I'm a demon, I can't break a deal once it's sealed.” Still suspicious, you nodded slowly.

“Look, I'm tired of being Crowley's hitman. I was thinking about striking out on my own soon anyway. So how's this: we do this, you don't fight me, and if I can make you come – and I'll be able to tell if you fake it – I won't kill you. You'll walk out the door alive and unharmed.” He paused, and his lips twisted into a familiar smirk. “Well, nothing permanent, anyway.”

Your mind raced, repeating his words over and over, trying to find a loophole. “But what about Crowley?” you asked. 

Dean shrugged. “I'll lie to him, tell him I killed you. You'll have to hide, obviously, quit your job and all that, but hey, you'll still be breathing.” He rolled his eyes when he saw you were still undecided, and leaned back down to bite at your neck. “Going once...going twice...”

“Okay!” you blurted out. “Yeah, okay, I'll do it.” You fought not to pull away as he leaned in for the kiss that would seal the deal, and closed your eyes as his lips pressed against yours.

They felt the same as they had years ago, and when his tongue flicked out to seek entrance, you instinctively opened your mouth and let him in. He plundered your mouth and you let him, lying passively under his weight, not wanting to participate but also not wanting to fight him and break the deal. The old attraction was still there, had been from the moment you saw him again, but overlaying it was the absolute terror you'd felt since the moment his eyes had flickered to black the first time.

Dean sat back and you could hear the frown in his voice. “Darlin', I'm gonna need a little more audience participation than that. I mean, it's in your best interest to let me make you feel good.”

He was right. You took a deep breath, then another, then opened your eyes and made contact with his. They were back to green now, the only hint of his demonic nature being the very faint scent of sulfur that swirled around him, and you reminded yourself that you needed him in a good mood. While he'd promised to let you leave unharmed, “nothing permanent” could mean quite a few painful things along with the more pleasant ones he'd meant.

“You're right,” you said, and nodded. “Let's try again.” Dean actually looked surprised for a moment before leaning back down and capturing your lips again. This time you kissed him back, sliding your tongue against his and sucking his bottom lip into your mouth, nipping it gently before letting it go.

When the two of you finally broke apart, you were breathing heavily and feeling like this might actually work. Dean, at first glance, seemed unaffected, but upon closer inspection you could tell that the circle of green around his pupils was steadily shrinking as his desire grew. “Clothes,” you growled, needing this to progress quickly before you lost your nerve.

Of course, Dean wasn't inclined to let you just get this over with. “Not so fast, sweetheart,” he purred, leaning down to lick a long stripe up your neck. “I wanna enjoy this.” You forced yourself to relax and submit to his ministrations as he kissed and nibbled along your neck, letting out a squeak of surprise and pain when he nipped your earlobe hard. As he worked his way down to your collarbone, exposed by your white silk shell, you were beginning to really enjoy the familiar sensation of his stubble prickling against the soft flesh of your throat. _After all,_ you thought as he sucked hickeys into your skin, _he is gorgeous, and it's not like I have to worry about James seeing them and finding out –_

With that thought, your libido was immediately doused in cold water. Dean sensed the change in your reactions and drew back, his mouth swollen and spit-slick from creating the marks on your neck. “Jesus, what is it this time?” he said, scowling and rolling his eyes. You bit your tongue to fight back tears and mutely shook your head, not trusting your voice. The ex-hunter's eyes slid to black as he repeated, “What's your problem this time?” When you still didn't respond, biting your tongue even harder and fighting to control your quivering lips, he snarled and grabbed your chin. 

Suddenly, there was a knife made of what looked to be some animal's jawbone pressed against your throat, and you gasped involuntarily. _Where the hell did that come from?_ “I'm not gonna ask a third time,” the demon said quietly, his already-bruising grip tightening on your face. “This is beginning to not be worth the effort.”

“I just -” you sobbed, then stopped and forced yourself to breathe in, and out, and in, and out, before trying again. “I just remembered that I don't have a fiance to go home to anymore.” Taking a chance and trying to salvage the deal, you looked up into his black eyes with an imploring look on your face. “Please, help me forget.”

Dean grinned fiercely, his eyes flicking back to green as he made the blade disappear. “I can do that.” His mouth descended on yours again, this time not giving you a chance to respond as he devoured your lips. Your burgeoning arousal roared back in force, and you pushed your hips up as best you could and let out a quiet whimper into his kiss.

Breaking away, he began making marks on the exposed skin of your chest again, no longer following the line of your clavicle, but instead in a seemingly random pattern. When his mouth reached the neckline of your top, he growled in frustration and ripped it down the center with one hand. You let out a soft gasp of surprise as he continued down the line of your breastbone and onto your stomach, stopping for a moment to nuzzle at your fabric-covered breasts. When he reached your bellybutton, he bit the soft skin just above it hard, and you gasped in pleasure-pain and jerked at your bonds. You ached to touch him, to wind your fingers into that dark blond hair and pull him back up to your lips so you could kiss him for as long as you wanted.

That thought promptly went out the window as Dean produced another knife out of nowhere, this one metal, and slid it between the cups of your bra. He jerked upwards, the fabric parting easily around the sharp blade, and flipped the cups to the side. “That was a front clasp, Dean,” you said, panting as he nuzzled the newly exposed skin.

He shrugged. “Doesn't matter, I'm gonna cut the straps anyway.” True to his word, he sliced the straps away from the cups as well, shredding the rest of your top while he was at it, then pulled the ruined fabric from under your body and tossed it to the side.

“You could have just untied my -” you began, then cut yourself off with a moan as Dean's lips closed around your left nipple. He sucked on it hard, making whatever you had been about to say fly out of your mind as you arched your back and pushed as much of your breast into his mouth as you could. When he pulled away, you whined at the loss and pouted at his smirking face.

“You are so beautifully responsive, you know that?” he said, bending down to swipe his tongue over your right nipple and chuckling as you whimpered. You barely registered that he was moving until he was sprawled on your right side, mouth still fastened to your breast, and his hand was drawing suggestive lines along the waistband of your black slacks.

You wriggled under him, trying to wordlessly suggest that he slide his hand a bit further down and he obliged, slipping his fingers deftly under the fabric and tracing them down the crease of your thigh. You spared a quick moment to close your eyes and thank whatever heavenly powers were listening that you were wearing decent underwear today, then briefly reconsidered that prayer. Perhaps thanking heaven that you'd worn pretty underwear since you were currently being ravished by a Knight of Hell was not the most suitable thing to do.

Your inappropriately celestial thoughts were cut off when Dean's fingers slid under your panties and along your slick folds, skimming your opening with gentle, feather-like touches. You gasped and thrust your hips up, aching for more contact, for those wonderful fingers to move just a little bit to where you desperately needed them. Almost as though the demon was reading your mind, he moved upward, slowly but surely, and you almost sobbed in relief as he set up a pattern of rapid circles around your clit.

Dean's talented fingers were going to bring you to orgasm in no time at all, if he kept this up. _Well, the conditions of the deal would be met and I'd be walking out of here,_ you managed to think through the haze of arousal that had taken over your mind. You were almost there – so close – 

Your eyes flew open and you cried out in loss as Dean pulled his hand out of your pants, bringing his fingers to his mouth and licking them clean with lewd joy. “Oh, I'm sorry, sweetheart,” he said with mock concern, “did you need something?” You clenched your teeth and threw your head back, trying to resist the urge to tell him to go fuck himself – or to beg for him to finish; you were having a hard time deciding which one was more tempting.

Dean laughed and got off the bed, shrugging off his red flannel and pulling his black t-shirt over his head. Distracted by the show in front of you, you almost forgot about your aborted orgasm, instead indulging yourself and drinking in the sight of all the golden skin and hard muscle being revealed as Dean removed his clothing. 

When he was down to his boxers, he climbed back on the bed and quickly unbuttoned your pants, jerking them down your legs. When he met the ropes securing your ankles to the bed, he frowned and quickly produced a knife and sliced through them, throwing the nylon strands and your slacks across the room. He hooked his fingers into the waistband of your underwear and slid them slowly over your hips, taking what felt like a century to remove them as you bit your lip and squirmed under him. You were left completely exposed, open to the demon's lustful gaze, and you blushed as he blatantly licked his lips. Unconsciously, you pulled your knees up, trying to hide your nudity from Dean's appreciative stare.

A frown quickly overtook his face, and he reached out and jerked your legs down. “Don't bother hiding from me, princess, I've seen it all before,” he said irritably, pinning your lower half to the bed with his body weight.

“Sorry,” you whispered, trying to relax. Surprisingly, Dean gave you a few moments to collect yourself before beginning to nip at your collarbone again, apparently trying to make sure that the hickeys he'd given you earlier were as dark as possible.

Within a few minutes, your brief attack of insecurity had faded and you were gasping and writhing under Dean's mouth as he kissed and licked his way down your torso again. As he made his way downward towards his ultimate goal, your legs began to spread without your conscious direction. Dean settled himself between them, his mouth curving in a smile against your skin, and you jumped and squeaked as he nipped at your hip and continued down. “Little wider, darlin',” he murmured against your inner thigh, and your heart raced as you spread your legs as far as you could.

At the first flick of Dean's tongue against your clit, you gasped and shoved your hips up against his mouth, but his big hands grabbed your ass and _slammed_ you back down on the bed. “Hold still,” he growled against your pussy, and you hissed as the vibrations rolled through the sensitive flesh. He continued licking and sucking, tracing circles around the tiny bundle of nerves, building you up and up and up until - 

He stopped. _The bastard stopped!_ “Dean,” you whimpered, “I need - ” Before you could finish he dove back in, making obscene slurping noises as he swiped his tongue along your opening, pressing tiny kisses to your clit, stopping just short of enough pressure or stimulation to tip you over the edge. He kept you on that cliff, that shining precipice, for what felt like hours before he abruptly, cruelly, pulled away again. “Oh God,” you mewled. “I need – you have to - ”

Dean looked up at you with those vivid green eyes. “I have to what, sweetheart?” he inquired mercilessly.

“I need to come!” you sobbed, twisting under him.

“Yeah?” Dean said, raising an eyebrow and standing up, leaving you bereft. “Beg me for it.” He shoved his boxers down his legs and kicked them off before climbing back on the bed and lowering himself down onto you, cock nudging at your slick folds. “Come on, darlin',” he whispered in your ear. “Just one word. One little, six-letter word. It's not that hard.” He thrust forward, just a little, and the thick head of his cock slipped inside you. You moaned and pushed your hips up, trying to get more, but instead the demon moved backwards and withdrew completely.

“Dean – God, I need to – you have to let me – Dean - ”

“As much as I enjoy you screaming my name, I need a little more, princess. What's the word I want?”

Finally you threw your head back and screamed, “Please! Please, Dean, I need to come, I have to -” His cock slammed into you with bruising force, cutting off the rest of your plea, and he quickly set a punishing pace. You wrapped your legs around his waist and met him thrust for thrust, gasping at the pain-pleasure each thrust gave to you.

His hips slammed into your pelvis and made you cry out, still reaching desperately for that elusive peak Dean had been withholding from you for the past hour. It seemed out of reach, despite how close you'd been, and you writhed under him and started begging again. “Dean, please, I need more, just a little, please!” 

He finally took pity on you and reached down between your bodies, rubbing his finger across your clit and making you see stars. “How's that?” he panted, hist thrusts getting harder and more brutal, and your only answer was a scream as you finally, _finally,_ came so hard you all but blacked out. 

You almost missed Dean growling into your neck and shuddering as he found his own climax, but you jerked back to awareness as he slowly pulled out of you. “Damn, baby, you're just as good a fuck as I remember,” he said, swiping his finger through the mess between your legs and making you shudder. “Makes me not want to let you go.”

A chill rolled through your body and you protested, “But we have a deal! You made me come – hell, I even begged you for it, just like you wanted – now you have to let me go!”

“I don't recall ever promising to let you go,” Dean said thoughtfully, wiping his slick finger across your thigh.

You were panicking now. “No! You did! You said you'd let me walk out the door, alive and unharmed!”

Dean grinned. “I did, didn't I? But I don't think I specified that you'd be alone, or that I wouldn't find you again, or hell, that I'd let you walk out that door any time in the next twenty years.”

Your blood went cold. _Oh God. Oh God oh God oh God he's right._ You'd been too caught up in the prospect of escape to make sure the deal was loophole free and now - 

“Cheer up, princess,” Dean said, leaning over you. He bent down and sank his teeth into your throat, leaving what was sure to be a spectacular hickey, as you started crying. When he came back up, his eyes were black. “Promise it'll be fun.”


End file.
